(4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester → (1-Bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester

HRID 238618Notes

Reaction equation

HRID 238618 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[Br:24]>C(OCC)(=O)C.[Pd].[Br-].[Zn+2].[Br-]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[Br:24]

Participants

5

Reactant 1

HCID 59326473(4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326528(1-Bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl esterYield 64.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (400 mg, 0.992 mmol) in ethyl acetate (10 mL) was added zinc bromide (670 mg, 2.978 mmol) and 10% palladium on carbon (40 mg) under a hydrogen atmosphere (balloon). After being stirred at room temperature for 1 hour, the resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC (gradient elution with 50-80% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes) to afford (1-bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester (200 mg, 64.4%) as a white solid.

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (gradient elution with 50-80% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes)

Sources & evidence

ORD record
ord-2a25c9a209c54508ac3c5d1b92d7b828
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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